


Picking Up The Pieces

by byepolarbear, Meowes, White_Rose_Trash



Category: RWBY
Genre: AU, Alternate Universe, Angst with a Happy Ending, Business Woman Weiss, Courtesan!Ruby, Cuddling & Snuggling, F/F, Fluff and Smut, Hurt/Comfort, Implied Non-Con, Prostitution, Whiterose, but it works out, its a bit heavy
Language: English
Status: Completed
Published: 2017-09-17
Updated: 2017-09-17
Packaged: 2018-12-30 17:12:32
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,123
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12113388
Author URL: https://archiveofourown.org/users/byepolarbear/pseuds/byepolarbear, https://archiveofourown.org/users/Meowes/pseuds/Meowes, https://archiveofourown.org/users/White_Rose_Trash/pseuds/White_Rose_Trash
Summary: It's just another job for Ruby as a high-end courtesan. She's surprised by how much money the girl has, but even more with how easy the girl breaks down all her barriers.





	Picking Up The Pieces

**Author's Note:**

> Hello!. Apologies for not posting a new chapter of CrossRoads, but White_Rose_Trash, here on AO3 and fanfiction.net, and Meowes, on fanfiction.net, and I worked on this together for a long time. I'm really excited for this fic and I hope you enjoy.!

Life had always been successful for Weiss, at least from the outside. She was the heir to one of the biggest companies in the world, a groundbreaking businesswoman, and immensely wealthy. The issue with Weiss lay within her personal life. She was happy with the money no doubt, but money could only provide so much. There were deeper, soulful needs she required. Love, happiness, and understanding; to name a few. Weiss had the world in her fingertips yet everything she desired was beyond this world. They resided where money could not reach and power could not influence. All these thoughts and more ran through Weiss’ head as she stared at herself in the mirror of her bathroom. Her outward appearance was immaculate as always. Perfect hair, perfect features all displayed with a light touch of makeup. Imperfections were removed and forgotten. However, on the inside, she was the opposite. She was empty. She was a machine who performed her duties and nothing more. She had nothing to go home to and no one to care for. Finding a partner wasn’t exactly difficult in her line of work, especially with when she held the wealth that so many coveted. Weiss held different preferences than most, the press would have an absolute field day if they knew of her attraction to women. As if she wasn’t busy enough with her work -- far too busy to find a partner anyway -- the effort that went into finding someone of the same sex that shared her preferences was beyond reason. Being busy didn’t prevent her life from becoming plagued by loneliness and sexual frustration. With the possession of money, however, there were solutions to this problem.There were rumors of this place you could go to ‘find these solutions’. A place by the name of “Adam’s Den”. These rumours had been continuously buzzing and meandering around Weiss. They tempted her to action. These temptations could no longer be ignored. Weiss had a few contacts that could get her in the door, and she had made arrangements for a high end ‘courtesan’ to pay her a visit tonight. Being immersed in the high-stakes world of business had lead to a detailed knowledge of society’s dark secrets.  
Ruby sighed as she stood outside her ‘clients’ penthouse. She expected another exhausting, perhaps rough night and it was really starting to wear on her. She knew that her client had money, but that was about it, something about preferring to keep the meeting as discrete as possible. Not unusual, really. Many clients had perverse and otherwise socially unacceptable tastes. Adam never dealt with anything too far off, but Ruby had still filled more than a few odd requests. Ruby remembered them all. Not in her conscious memory, but her subconscious reminded her of every thrust and every painful hand forcing itself upon her. She couldn’t dwell on these thoughts for long. She had to appear willing and happy for her client. Adam expected nothing less. Ruby knocked at the door, her eyes wandering through the lavishly decorated hallway. It wasn’t long before the door opened, and an unrecognizable voice hissed  
“Get in quick, I don’t need anyone seeing that you’re here”  
Ruby stepped in quickly as she was asked, and was greeted by the sight of a tall, elegant woman with long, shining white hair. She looked familiar, but Ruby didn’t care to linger on it, it really didn’t matter. She resisted the urge to breathe a sigh of relief. Female clients tended to be in the very least gentler than males, and it made the night easier on Ruby. Unfortunately they were rare. Rare enough to have Ruby dreading this night slightly less and for her not to care what familiarity she may have. As she was thinking, the woman began to frantically close the door behind her while looking around in a panic.

“I assume you payed ahead?”  
This was a service and like all services it required money.  
“Of course. You can check with whomever handles your money if you don’t believe me. Now, we can’t have anyone see us together. Everything that happens inside this room stays inside this room. Understand?”  
“Yes, ma’am. My services are 100% confidential. No need to worry” She replied automatically.  
Weiss breathed a sigh of relief. “Also, no need for formalities, you can just call me Weiss.”  
Ruby’s eyes flickered for a second in recognition but quickly returned to normal. It didn’t matter who this woman was, she had a job to do, and nothing would change that.  
Ruby gave her what she hoped looked like a genuine smile. “I’m Ruby. I need just a moment to change and then we can begin, sound good?”  
Weiss tried not to sound too excited, but she really needed this tonight. “Absolutely, take all the time you need.”  
Ruby stepped into the equally decorated bathroom and shut the door. She took just a moment to glance at her surroundings, stunned at just how much money this woman had. She sighed as she looked in the mirror. Her silver eyes were dulled in exhaustion, and there were barely visible circles under them. She managed to cover up the circles with a bit of makeup, but there was little she could do to patch up her mood besides taking a few deep breaths. She was supposed to be confident, sexy, and seductive. With a final shake of her head and deep sigh, she opened up the door.  
Weiss had figured she should undress while Ruby changed, and she sat underneath the blankets on her bed, slightly chilled by the cool air on her skin. Weiss gave an honest effort not to stare when Ruby walked out, but it was no use. Her supple thighs were highlighted by stockings as red as her namesake, and those abs. Her whole body shuddered at the thought. She had spent years denying her attraction to women, but she never would have been able to deny how much Ruby made her want to drool. She was beautiful, sexy, and...and… she was climbing over Weiss now, her modest breasts now pushing against Weiss’ body.  
Ruby could tell Weiss wasn’t quite used to this situation as she blushed and stared the whole time, stuttering any necessary responses. It didn’t matter though, while she was at work, Ruby put on a completely different face. She had done it so many times now that it was almost automatic. She climbed on top of Weiss’ blushing form, biting down softly on her neck while grazing her hands over Weiss’ soft stomach.  
“Let’s make sure you get your money’s worth” Ruby whispered with a particularly rough nibble.  
“I feel like I already have, your body is perfect, and your hands feel so good” Weiss responded with a pleased shudder.  
“Oh? Well imagine how good my mouth feels” Ruby said with a hot breath, tugging lightly on Weiss’ earlobe, and the white haired girl whimpered.  
Wordlessly, Ruby trailed down Weiss’ form. The fact that Weiss was equally as attractive to Ruby as she seemed to be to Weiss made it easier. She could at least enjoy how hot the girl’s voice seemed to be, and the feeling of her skin. As Ruby reached the aching flesh between Weiss’ legs, she began to lightly run two fingers over the moist folds, drawing a quick gasp followed by a soft whine from the businesswoman.  
“Nggh. Tongue. Please.” Weiss moaned.  
Weiss’ wish was Ruby’s command, and she painted a slow stroke with her tongue up to the top of Weiss’ center. With a soft cry Weiss’ hands tangled in the short brunette hair of the courtesan, and she gave a solid rock of her hips into the euphoric touch. Ruby pressed her lips against the top half of Weiss’ center, giving it a soft suck as her tongue began to work the throbbing nub at the top.  
Weiss writhed in pure pleasure. “Gods yes, you’re so-mmmm-good, haah.”  
Ruby kept up her actions diligently, beginning to circle Weiss’ clit before flicking the sensitive underside softly. She repeated this pattern over and over, and Weiss just wouldn’t stop squealing her praise. She really couldn’t hold back, she needed her release. This girl wasn’t just a pretty face, she knew how to work Weiss just right, making her whole body hum in pleasure.  
“Hnng. Fuuck, Ruby don’t stop, please don’t stop.” Weiss panted, her face flush with pleasure.  
Ruby kept up exactly that same action, knowing she had found just the perfect motion to bring Weiss to her climax. She was surprised at how gentle the girl was, massaging her scalp softly. She was used to being forced closer, and demands for more pressure and to go faster, but Weiss seemed to enjoy everything, moaning sweet praise at every action. It was a well welcome change, and for once she didn’t mind pleasing someone else quite as much.  
“Fuck yes, yes yes yes, Uhnnnn” Weiss’ climax finally rocked her, her hips bucking excitedly, and her breath turning into short pants.  
Ruby felt soft hands gently push her away, and she settled on a sensual kiss on Weiss’ thigh. Normally she saved the gentle gestures, but she was appreciative of Weiss’ soft and praising touch.  
Weiss felt like she had just come down from one of the best orgasms of her life, and already the tongue that brought her there was back between her legs, and she just let out a low moan, her limbs going limp. “Ohh God”  
Ruby figured Weiss would want another right away, most everyone did, and it didn’t look like she was wrong, the businesswoman’s hips already pressing eagerly into her tongue once again. She focused her attention on the button of pleasure at the top once again, slowing her circles and softening her flicks ever so slightly to accommodate for Weiss’ increased sensitivity.  
Weiss could only groan and writhe, she couldn’t focus on anything but the heavenly feeling between her legs, Ruby’s tongue was so soft, and she had this perfect pressure that caused complete euphoria to course through her body. She tried to drag out her climax, but when Ruby began to hum quietly while sucking firmly, she had nowhere to go except over the edge, moaning endless praise of Ruby’s actions.  
Ruby felt Weiss’ whole body shudder with climax, and began to lightly tease her nub to extend it, feeling her legs twitch and a groan of pleasure leave her throat. She felt hands grab her shoulders after a few seconds and she winced, expecting Weiss to push her down again, but instead the white haired woman just brought Ruby face to face with her, and enveloped her arms around Ruby. Her hand quickly trailed down Ruby’s form, and sunk beneath her panties. Ruby tightened noticeably, once again expecting harsh penetration, but instead Weiss just began lightly running her fingers through Ruby’s folds, and the short haired girl shuddered. For once, this actually felt good. She let out a soft whimper, and Weiss chuckled.  
“You did such an amazing job, you deserve some too” Weiss whispered with a soft nibble on Ruby’s earlobe.  
“Most people don’t pay to-hnnn-pleasure me the whole night” Ruby managed to get out.  
“Well then most people don’t deserve such a beautiful guest do they” Weiss whispered with a hot breath.  
Ruby just moaned in response, she never wanted this girl to stop talking, she swore that Weiss’ voice had a direct line straight between her legs, making her shudder in arousal.  
“God, you’re so soft down there, how does this feel?” Weiss asked, her head resting on Ruby’s shoulder now, breathing directly into her ear.  
“Mmmm soo good, It’s been so long since someone has touched me.”  
“That’s a shame, they don’t know what they’re missing out on, you sound and feel amazing. I want to feel you. Hear you. Make you come” Weiss whispered, spacing out the last words with wet kisses on the base of Ruby’s neck. At the same time, her middle finger found Ruby’s sensitive button and began to tease it, up and down and back and forth.  
The combination of Weiss’ voice and her skilled fingers was too much. It had been so long since Ruby had been given any real pleasure, and this girl sure was showing her the time of her life.  
“Hnnn-Weiss I’m soo close” Ruby moaned shakily  
“Good, you deserve this, stop being so tense and enjoy this, you’re allowed to feel good.” Weiss said in content.  
Ruby relaxed the muscles she didn’t know she was tensing, and with a soft cry her climax was allowed to reach her.  
Weiss merely buried her head in Ruby’s neck, enjoying the subtle twitches of her body, and the sweet sound of her moans as she rode out her finish.  
Catching her breath, Ruby expected Weiss to push her back down between her legs, or to climb on top of her and ask for more, but the girl was just full of surprises as she pulled Ruby closer to her, curling around Ruby and sighing softly.  
“Ummm, what are you doing?” Ruby asked shakily  
“I’m...cuddling with you?” Weiss said nervously “Is that okay?”  
“That’s fine it’s just that m-most people don’t pay for a night of sexual favours with a scantily clad woman just to cuddle with her. You know you still have me for the rest of the night.” Ruby responded.  
“Can I be honest with you?” Weiss said hesitantly  
Ruby didn’t know why Weiss would want to share anything with her, but she figured that she had been nice enough for Ruby to justify listening to whatever she had to say.  
“Sure”  
“Being famous in business makes it really hard to want to be with women, between the press and the difficulty of finding a partner, it gets really hard sometimes. I get lonely and just...cuddling feels better than sex right now.” Weiss finished with a soft kiss on Ruby’s neck that she hoped the girl didn’t mind too much.  
Unknowingly, Weiss had slowly been chipping away at Ruby, causing cracks in her facade, and with that last motion she had broken it entirely, and the torrents of emotion came rushing out. Ruby broke into a bout of sobs, and instantly Weiss’ arms squeezed tight around her. “What’s wrong, are you okay?”  
Ruby shook her head and tried to wriggle from Weiss’ arms. “You didn’t pay to see me like this, I’ll just leave and have A-Adam cut the bill. I’m so sorry.”Weiss squeezed her tight against her body, and Ruby just didn’t have the strength to try to get out. “It’s okay, just tell me what’s wrong, I don’t want to see you cry.” Weiss said softly, as if the words could scare Ruby away.  
“Why do you care!” Ruby sobbed loudly, tears streaming down her face.  
“Shhh” Weiss whispered, kissing Ruby’s neck softly. If she was being honest with herself, she didn’t know why she cared either, maybe it was just her loneliness finally getting to her, but something about this girl just made her want to protect her, to make sure nothing could ever hurt her again. “I care because I could see how hurt you were in your eyes, I could tell no one had treated you with respect. It breaks my heart, you’re too pretty and sweet to deserve this. Just let it out, you’re safe with me.”  
Ruby didn’t know why she felt like she could trust this girl, but she needed to get it out, she couldn’t bottle it up any longer.  
“When I was seven my mother died, and my dad, he tried so hard to help us out, but a few months after I turned 18 he just collapsed. Years of working 2-3 jobs took its toll on him, and all he can do is lay on the couch in pain now. I know that if he could help at all he would.” Ruby paused to break into a fresh bout of sobs, and Weiss just continued to hold her, letting her finish what she needed to say. “My dad and I didn’t want me to do this, but the pay is good, and there wasn’t any other option.”  
Weiss interrupted. “I’m so sorry Ruby, you don’t deserve this.”  
Ruby just continued. “You don’t understand how hard this is, I have to cover up the bruises from being hit and smacked around, when you called my name that was the first time since I can remember that I haven’t been called just a slut, a whore, or a worthless bitch. I just don’t know how much longer I can do it. I’m so broken and disgusting. I can remember how each of them felt inside me and how horrible it makes me feel. I have to just sit in the shower and cry, trying to clean off all the disgusting things that I have to do every night. I keep trying to wash away the pain but it's still there every day. The worst part is, I have to keep doing it, there’s just no way out. I can’t stop. If I do, I’ll be homeless and my dad will probably die. I don’t think I’ll be able to take it if both my parents die, but the thought of working this awful job for another day makes me sick.”  
Weiss wished she could just squeeze all the hurt out of the girl, to make everything better with a caress of her hand and a kiss on her lips. “I’m so sorry Ruby” she repeated “Just let it all out, I’m here for you. I’m sorry.”  
Ruby continued after gaining her composure. “And then along comes this pretty girl, and she’s so gentle and treats me with just an ounce of respect. She makes me feel like I had value. Like I wasn't just a piece of meat for those...animals. She gave me pleasure for the first time that I can remember. She starts to chip away at the mask I’ve created and just when I think I can hold my composure. She holds me and kisses me and...after being treated like I’m beautiful, I just don’t know if I can go back. Thank you, Weiss, I don’t know why you care, but please don’t stop.”  
“I know you don’t have any reason to trust me, but I promise I’m going to help you. Just relax okay? You’re exhausted, get some rest and I still have you for a few hours in the morning, we can talk then.”  
“Thank you so much, Weiss.” Ruby whispered before snuggling into Weiss’ arms. They felt so warm. It was what she needed for now.

**Author's Note:**

> Hope you enjoyed. Please review! Don't be shy as I love reading them! Take care and until next time!


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